维生素A酸、异维生素A酸双酯的合成与结构表征  

Synthesis and Characterization of all-trans-Retinoic Acid and 13-cis-Retinoic Acid Diester Derivatives

作　　者：党奎峰[1] 陈静[1] 赵娜[1] 段军飞[1] 向建南[1] 

机构地区：[1]湖南大学化学化工学院,湖南长沙410082

出　　处：《化学世界》2006年第4期228-231,共4页Chemical World

基　　金：湖南省自然科学基金(03JJY3016);国家自然科学基金(20472018)资助

摘　　要：以异维生素A酸为原料,二环己基碳酰亚胺(DCC)为脱水剂,4-二甲氨基吡啶(DMAP)为催化剂,设计合成了结构新颖,具有潜在生物活性的化合物4a(异维生素A酸对苯二酯),产率达到87.6%。优化条件为:异维生素A酸与对苯二酚摩尔比为2.02∶1,反应时间4 h,DCC滴加速度为0.5滴/秒。在此条件基础上由维生素A酸、异维生素A酸合成了其它5种双酯。并将4a进一步结构修饰,得到异维生素A酸在人体内代谢氧化物的衍生物,产率达到75.3%。以1H1、3C NMR和MS对它们的结构进行了表征。With dieyelohexylearbodiimide （DCC） as reagent and 4-dimethylaminopyridine （DMAP） as catalyst, the compound 4a （p-phenylene di-13-c/s-retinoates） with novel structures and potential bioaetivity was synthesized from 13- c/s-retinoie add,and a yield of 87.6% was obtained,The optimized conditions are ：2.02 portions of 13-c/s-retinoie acid and one portion of quinol were added into a flask, stirring 4 h after DCC was added at a rate of 0. 5 drop per second. Other five diesters were synthesized from all-trans-retinoie acid and 13-c/s-retinoie acid under similar conditions. Then 4a was modified to obtain the anologue of metabolization in the hotly, and a yield of 75.3 % was obtained. Their structures were characterized by ^1H,^13C NMR and MS.

关 键 词：维生素A酸 异维生素A酸 二羟基化合物 双酯 合成 表征 

分 类 号：O623.624[理学—有机化学]